US5614651A - 14α-hydroxy-4-androstene-3,6,17-trione hydrate crystal and process for producing same - Google Patents

14α-hydroxy-4-androstene-3,6,17-trione hydrate crystal and process for producing same Download PDF

Info

Publication number: US5614651A
Authority: US; United States
Prior art keywords: type crystal; androstene; hydroxy; crystal; trione
Prior art date: 1993-05-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

US08/247,778

Other languages

English (en)

Inventor

Kazuo Ohtsuki

Akikazu Mitsunobu

Yoshihiro Imaizumi

Nobuyoshi Honda

Satoshi Inoue

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Snow Brand Milk Products Co Ltd

Original Assignee

Snow Brand Milk Products Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-05-28

Filing date

1994-05-23

Publication date

1997-03-25

1994-05-23 Application filed by Snow Brand Milk Products Co Ltd filed Critical Snow Brand Milk Products Co Ltd

1994-05-23 Assigned to SNOW BRAND MILK PRODUCTS CO., LTD., NIPPON KAYAKU KABUSHIKI KAISHA reassignment SNOW BRAND MILK PRODUCTS CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HONDA, NOBUYOSHI, IMAIZUMI, YOSHIHIRO, INOUE, SATOSHI, MITSUNOBU, AKIKAZU, OHTSUKI, KAZUO

1995-05-30 Priority to US08/453,875 priority Critical patent/US5648507A/en

1996-12-24 Assigned to SNOW BRAND MILK PRODUCTS, CO., LTD. reassignment SNOW BRAND MILK PRODUCTS, CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NIPPON KAYAKU KABUSHIKI KAISHA

1997-03-25 Application granted granted Critical

1997-03-25 Publication of US5614651A publication Critical patent/US5614651A/en

2014-05-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000013078 crystal Substances 0.000 title claims abstract description 102
UKVVNEHFNYKGMX-KIVPVIKRSA-N (8r,9s,10r,13s,14r)-14-hydroxy-10,13-dimethyl-2,7,8,9,11,12,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,6,17-trione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@]4(O)[C@@H]3CC(=O)C2=C1 UKVVNEHFNYKGMX-KIVPVIKRSA-N 0.000 title claims abstract description 26
238000000034 method Methods 0.000 title abstract description 13
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 14
230000015572 biosynthetic process Effects 0.000 abstract description 3
238000003786 synthesis reaction Methods 0.000 abstract description 3
102000004190 Enzymes Human genes 0.000 abstract description 2
108090000790 Enzymes Proteins 0.000 abstract description 2
230000004071 biological effect Effects 0.000 abstract description 2
230000002401 inhibitory effect Effects 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000003960 organic solvent Substances 0.000 description 15
239000000243 solution Substances 0.000 description 14
239000003814 drug Substances 0.000 description 10
229940079593 drug Drugs 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 7
150000001875 compounds Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 4
238000005259 measurement Methods 0.000 description 4
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
UDHAKZRCGHAPAZ-NFBMXZEVSA-N (6r,8r,9s,10r,13s,14r)-6,14-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@]4(O)[C@@H]3C[C@@H](O)C2=C1 UDHAKZRCGHAPAZ-NFBMXZEVSA-N 0.000 description 3
238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000013112 stability test Methods 0.000 description 3
238000000967 suction filtration Methods 0.000 description 3
238000005303 weighing Methods 0.000 description 3
-1 14α-hydroxy-4-androstene-3,6,17-trione anhydride Chemical class 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
235000002597 Solanum melongena Nutrition 0.000 description 2
244000061458 Solanum melongena Species 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
235000010333 potassium nitrate Nutrition 0.000 description 2
239000004323 potassium nitrate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000011160 research Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
241001019659 Acremonium <Plectosphaerellaceae> Species 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
206010056740 Genital discharge Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 1
229960005471 androstenedione Drugs 0.000 description 1
AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
238000001055 reflectance spectroscopy Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1

Images

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group

Definitions

the 14 ⁇ -hydroxy-4-androstene-3,6,17-trione is obtained as a crystal by distilling off the solvent from the organic solvent solution.
the above patent publication mentions that thus obtained crystal is white, but strictly speaking this is yellow.
the present invention provides 14 ⁇ -hydroxy-4-androstene-3,6,17-trione hydrate crystals and a process for producing same.
the detail of the present invention are as follows.
FIG. 5 shows the charts of the thermal analyses of the ⁇ -type crystal.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Battery Electrode And Active Subsutance (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

US08/247,778 1993-05-28 1994-05-23 14α-hydroxy-4-androstene-3,6,17-trione hydrate crystal and process for producing same Expired - Fee Related US5614651A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US08/453,875 US5648507A (en)	1993-05-28	1995-05-30	14α-hydroxy-4-androstene-3,6,17-trione hydrate and process for producing same

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP5-151320		1993-05-28
JP15132093		1993-05-28

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
US08/453,875 Division US5648507A (en)	1993-05-28	1995-05-30	14α-hydroxy-4-androstene-3,6,17-trione hydrate and process for producing same

Publications (1)

Publication Number	Publication Date
US5614651A true US5614651A (en)	1997-03-25

Family

ID=15516058

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
US08/247,778 Expired - Fee Related US5614651A (en)	1993-05-28	1994-05-23	14α-hydroxy-4-androstene-3,6,17-trione hydrate crystal and process for producing same
US08/453,875 Expired - Fee Related US5648507A (en)	1993-05-28	1995-05-30	14α-hydroxy-4-androstene-3,6,17-trione hydrate and process for producing same

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
US08/453,875 Expired - Fee Related US5648507A (en)	1993-05-28	1995-05-30	14α-hydroxy-4-androstene-3,6,17-trione hydrate and process for producing same

Country Status (9)

Country	Link
US (2)	US5614651A (cs)
EP (1)	EP0626388A3 (cs)
CN (1)	CN1100101A (cs)
AU (1)	AU673593B2 (cs)
CA (1)	CA2124382A1 (cs)
CZ (1)	CZ128394A3 (cs)
HU (1)	HUT67804A (cs)
PL (1)	PL303609A1 (cs)
RU (1)	RU94018528A (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20090203741A1 (en) *	2006-07-14	2009-08-13	Astellas Pharma Inc.	Crystals of benzoxadiazole derivative

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996040445A1 (en) *	1995-06-07	1996-12-19	Owens Richard L	Article for applying and spreading viscous material and method thereof
CN1324042C (zh) *	2002-11-08	2007-07-04	株式会社钟化	麦角甾醇的分离方法
CN103073608B (zh) *	2013-02-26	2014-09-03	昆明理工大学	雄甾-4,6,8（9）,13（14）-四烯-3,11,16-三酮及其应用
CN103073607B (zh) *	2013-02-26	2014-09-03	昆明理工大学	12β-羟基雄甾-4,6,8（9）,13（14）-四烯-3,11,16-三酮及其应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4975368A (en) *	1987-02-06	1990-12-04	Snow Brand Milk Products Co., Ltd.	Novel androst-4-ene-3,17-dione derivatives and method for preparing same
US5098535A (en) *	1989-02-07	1992-03-24	Snow Brand Milk Products Co., Ltd.	Process for preparing 14-α-hydroxy-4-androstene-3,6,17-trione

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0368596A (ja) *	1989-08-09	1991-03-25	Snow Brand Milk Prod Co Ltd	１４α‐ヒドロキシ‐４‐アンドロステン‐３，６，１７‐トリオンの製造方法
JPH0576387A (ja) *	1991-07-22	1993-03-30	Snow Brand Milk Prod Co Ltd	１４α− ヒドロキシ−４− アンドロステン−３，６，１７−トリオンの新規製造方法

1994
- 1994-05-18 EP EP94107654A patent/EP0626388A3/en not_active Ceased
- 1994-05-23 AU AU63257/94A patent/AU673593B2/en not_active Ceased
- 1994-05-23 US US08/247,778 patent/US5614651A/en not_active Expired - Fee Related
- 1994-05-25 CZ CZ941283A patent/CZ128394A3/cs unknown
- 1994-05-26 PL PL94303609A patent/PL303609A1/xx unknown
- 1994-05-26 CA CA002124382A patent/CA2124382A1/en not_active Abandoned
- 1994-05-27 CN CN94105583A patent/CN1100101A/zh active Pending
- 1994-05-27 HU HU9401594A patent/HUT67804A/hu unknown
- 1994-05-27 RU RU94018528/04A patent/RU94018528A/ru unknown
1995
- 1995-05-30 US US08/453,875 patent/US5648507A/en not_active Expired - Fee Related

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4975368A (en) *	1987-02-06	1990-12-04	Snow Brand Milk Products Co., Ltd.	Novel androst-4-ene-3,17-dione derivatives and method for preparing same
US5098535A (en) *	1989-02-07	1992-03-24	Snow Brand Milk Products Co., Ltd.	Process for preparing 14-α-hydroxy-4-androstene-3,6,17-trione

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Remmington s Pharmaceutical Sciences, 15th edition, 1975, p. 1358. *
Remmington's Pharmaceutical Sciences, 15th edition, 1975, p. 1358.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20090203741A1 (en) *	2006-07-14	2009-08-13	Astellas Pharma Inc.	Crystals of benzoxadiazole derivative
US8278333B2 (en)	2006-07-14	2012-10-02	Astellas Pharma Inc.	Crystals of benzoxadiazole derivative

Also Published As

Publication number	Publication date
EP0626388A2 (en)	1994-11-30
HU9401594D0 (en)	1994-08-29
AU6325794A (en)	1994-12-01
CA2124382A1 (en)	1994-11-29
PL303609A1 (en)	1994-12-12
AU673593B2 (en)	1996-11-14
EP0626388A3 (en)	1996-06-19
RU94018528A (ru)	1996-04-10
HUT67804A (en)	1995-05-29
CN1100101A (zh)	1995-03-15
CZ128394A3 (en)	1995-11-15
US5648507A (en)	1997-07-15

Legal Events

Date	Code	Title	Description
1994-05-23	AS	Assignment	Owner name: SNOW BRAND MILK PRODUCTS CO., LTD., JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:OHTSUKI, KAZUO;MITSUNOBU, AKIKAZU;IMAIZUMI, YOSHIHIRO;AND OTHERS;REEL/FRAME:007016/0574 Effective date: 19940518 Owner name: NIPPON KAYAKU KABUSHIKI KAISHA, JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:OHTSUKI, KAZUO;MITSUNOBU, AKIKAZU;IMAIZUMI, YOSHIHIRO;AND OTHERS;REEL/FRAME:007016/0574 Effective date: 19940518
1996-12-24	AS	Assignment	Owner name: SNOW BRAND MILK PRODUCTS, CO., LTD., JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:NIPPON KAYAKU KABUSHIKI KAISHA;REEL/FRAME:008286/0167 Effective date: 19961217
2000-10-17	REMI	Maintenance fee reminder mailed
2001-03-25	LAPS	Lapse for failure to pay maintenance fees
2001-05-29	FP	Lapsed due to failure to pay maintenance fee	Effective date: 20010325
2018-01-25	STCH	Information on status: patent discontinuation	Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

Publication	Publication Date	Title
EP0410389B1 (de)	1995-03-15	Indolocarbazol und dessen Verwendung
US6022985A (en)	2000-02-08	Process for the preparation of 4-acetoxy-2α-benzoyloxy-5β, 20-epoxy-1, 7β-10β-trihydroxy-9-oxo-tax-11-en-13α-yl(2R,3S)-3-tert-b utoxy-carbonYlamino-2-hydroxy-3-phenylpropionate trihydrate
US4297271A (en)	1981-10-27	Guaiaconic acid A from guaiac resin
NO339927B1 (no)	2017-02-13	Krystaller av morfinanderivat og fremgangsmåte for fremstilling derav
KR20000048520A (ko)	2000-07-25	올란자핀의 제조 방법 및 그 중간체
US5614651A (en)	1997-03-25	14α-hydroxy-4-androstene-3,6,17-trione hydrate crystal and process for producing same
Simons Jr et al.	1979	Fluorescent chemoaffinity labeling. Potential application of a new affinity labeling technique to glucocorticoid receptors
Rosenthal	1973	The preparation and colorimetric analysis of L-canaline
IL29438A (en)	1971-02-25	Process for producing alpha-6-deoxytetracyclines
AU597136B2 (en)	1990-05-24	Method for preparing crystalline cefadroxil monohydrate
JPH0613557B2 (ja)	1994-02-23	テイコプラニン因子ａ▲下２▼成分１をテイコプラニン因子ａ▲下２▼成分３に転化する方法
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RU2132841C1 (ru)	1999-07-10	Способ очистки окситетрациклина и промежуточный продукт
Tischler et al.	1974	Rifamycin derivatives as inhibitors of a ribonucleic acid instructed deoxyribonucleic acid polymerase function. Effect of lipophilicity
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JPS58172399A (ja)	1983-10-11	ムラミルトリペプチド誘導体
Daniels et al.	1953	169. Studies in peroxidase action. Part VIII. The oxidation of p-chloroaniline. A reaction involving dechlorination
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JPH02163099A (ja)	1990-06-22	酵素触媒反応達成法
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SI9300002A (sl)	1994-09-30	Postopek in intermediat za čiščenje oksitetraciklina